α-Arylamino Diazoketones: Diazomethane-Loading Controlled Synthesis, Spectroscopic Investigations and Structural X-ray Analysis

Laura Castoldi, Laura Ielo, Wolfgang Holzer, Gerald Giester, Alexander Roller, Vittorio Pace (Corresponding author)

Publications: Contribution to journalArticlePeer Reviewed

Abstract

Primary and secondary a- halomethyl diazoketones generated via Arndt- Eistert chem. with min. loading of diazomethane efficiently alkylate arom. amines in the presence of calcium oxide to furnish the corresponding a- arylamino diazoketones under full chemocontrol. Such a simple inorg. acid scavenger fully neutralizes the hydrohalic acid formed during the nucleophilic displacement which otherwise would immediately react to produce the corresponding a- haloketone. The methodol. can be further exploited in analogous acylation- type processes on secondary arylamino diazoketones. In depth spectroscopic (1H, 13C and 15N- NMR) and crystallog. analyses document interesting structural features of these previously unknown diazo derivs.
Original languageEnglish
Pages (from-to)4336-4347
Number of pages12
JournalThe Journal of Organic Chemistry
Volume83
Issue number8
Early online date16 Mar 2018
DOIs
Publication statusPublished - Apr 2018

Austrian Fields of Science 2012

  • 104015 Organic chemistry
  • 104026 Spectroscopy
  • 301207 Pharmaceutical chemistry
  • 105113 Crystallography

Keywords

  • AMINO-ACIDS
  • ASYMMETRIC-SYNTHESIS
  • CHEMISTRY
  • CONTINUOUS-FLOW SYNTHESIS
  • DIAZO-COMPOUNDS
  • GENERATION
  • KETONES
  • NUCLEAR-MAGNETIC-RESONANCE
  • ORGANIC-SYNTHESIS
  • STEREOSELECTIVE-SYNTHESIS

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